WO2007124803A1

WO2007124803A1 - Water-based pigment preparation

Info

Publication number: WO2007124803A1
Application number: PCT/EP2007/001711
Authority: WO
Inventors: Björn FECHNER; Uwe Bechtold; Andrea BÖHMER
Original assignee: Clariant International Ltd
Priority date: 2006-04-27
Filing date: 2007-02-28
Publication date: 2007-11-08
Also published as: ES2335547T3; AR060821A1; DE102006019553A1; JP2009534506A; JP5008719B2; US20090095202A1; US7938900B2; BRPI0710901A2; DE502007002424D1; CN101400749A; EP2013299B1; EP2013299A1; BRPI0710901B1; CN101400749B

Abstract

The invention relates to an aqueous pigment preparation comprising (A) at least one organic and/or inorganic pigment, (B) dispersants and/or surfactants, (C) a trihydric or higher polyhydric alkoxylated alcohol, (D) a polyglycol alkyl ether, (E) if desired, hydrotropic oligomers and/or polymers, (F) if desired, fats, oils or fatty acids, (G) if desired, further additives typical in the preparation of aqueous pigment dispersions, and (H) water.

Description

description

Water-based pigment preparation

The present invention relates to water-based

Pigment preparations or dispersions, process for their preparation, their use for coloring natural and synthetic materials, in particular aqueous paints, dispersion and enamel paints of all kinds.

Known and commercially available are a variety of pigment preparations for coloring aqueous paints, dispersion and enamel paints. Examples thereof are contained in EP-A-0 735 109, WO 03/006 556 or EP-A-1 049 745 (US Pat. No. 6,478,866 B1). Usually anionic, cationic, amphoteric or nonionic dispersants with surfactant character, optionally also in macromolecular form, are used in order to physically stabilize the pigment particles finely in an aqueous medium. In addition, conventional pigment preparations generally also contain various additives in addition to the surfactants or dispersants, such as wetting agents, thickeners, preservatives, viscosity stabilizers, fillers and retention aids. The retention agents, often called anti-dryness additives, ensure that the product does not dry out or dries before use. For this purpose, low molecular weight, hygroscopic compounds such as glycols are often used, however, which entail the disadvantage of evaporating out of the application medium. Therefore, they are considered VOC (volatile organic compounds) and are increasingly regulated by the legislature. According to WO 03/006 556 and EP-A-0 585 571, VOC-free pigment preparations contain high molecular weight non-volatile oligomers or polymers such as, for example, polyether polyols (polyglycols).

However, hygroscopic non-volatile oligomers and polymers remain in the application medium for a long time. The retention of these substances has some disadvantages. For example, if an aqueous dispersion paint with a Pigment preparation is colored, containing such hygroscopic non-volatile compounds, the paint gets a slightly hygroscopic, sticky character. An increased water absorption is the result.

The present invention was therefore based on the object, aqueous

To provide pigment preparations that are dry-resistant but also VOC-free. When coloring, you must not change the performance properties of the emulsion paints, so that a tack-free surface is formed, which also has a low water absorption compared to the non-colored system.

It has surprisingly been found that certain polyalkylene glycols defined below in combination with polyglycol alkyl ethers fulfill the abovementioned object, if appropriate with fats and / or oils or further additives.

The present invention relates to aqueous pigment preparations containing

(A) at least one organic and / or inorganic pigment, (B) dispersants and / or surfactants,

(C) a trihydric or higher alkoxylated alcohol which is preferably branched, in particular star-branched,

(D) a polyglycol alkyl ether,

(E) optionally hydrotrope oligomers and / or polymers, (F) optionally fats, oils or fatty acids,

(G) optionally further customary for the preparation of aqueous pigment dispersions additives, and (H) water.

Preferred pigment preparations contain from 5 to 80% by weight, for example from 10 to 70% by weight, of component (A).

Preferred pigment preparations contain from 0.1 to 30% by weight, for example from 2 to 15% by weight, of component (B). Preferred pigment preparations contain from 0.1 to 30% by weight, for example from 3 to 15% by weight, of component (C).

Preferred pigment preparations contain from 0.1 to 20% by weight, for example from 1 to 10% by weight, of component (D).

Particularly preferred pigment preparations comprise component

(A) 5 to 80% by weight, for example 10 to 70% by weight,

(B) 0.1 to 30% by weight, for example 2 to 15% by weight,

(C) 0.1 to 30% by weight, for example 3 to 15% by weight, (D) 0.1 to 20% by weight, for example 1 to 10% by weight,

(E) 0 to 20% by weight, for example 0.1 to 10% by weight,

(F) 0 to 10% by weight, for example 0.1 to 7% by weight,

(G) 0 to 30% by weight, for example 0.1 to 5% by weight, and (H) the remainder water, in each case based on the total weight of the pigment preparation.

In the case that one or more of the components (E), (F) and (G) are present, their minimum concentration is independently of each other suitably at least 0.01 wt .-%, preferably at least 0.1 wt .-%, based on the Total weight of the pigment preparation.

The component (A) of the pigment preparation according to the invention is a finely divided organic or inorganic pigment or a mixture of various organic and / or inorganic pigments. The component (A) may also be a dye which is insoluble in certain solvents and has this pigment character. The pigments can be used both in the form of dry powder and as water-moist press cake.

Suitable organic pigments are monoazo, disazo, laked azo, β-naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigments and polycyclic pigments such as phthalocyanine, quinacridone, perylene, perinone , Thioindigo, anthanthrone, anthraquinone, flavanthrone, Indanthrone, isoviolanthrone, pyranthrone, dioxazine, quinophthalone, isoindolinone, isoindoline and diketopyrrolopyrrole pigments or carbon blacks. Of the said organic pigments, those which are as finely divided as possible for the preparation of the preparations are particularly suitable, with preferably 95% and particularly preferably 99% of the pigment particles having a particle size <500 nm. Depending on the pigment used, the morphology of the pigment particles may differ greatly, and accordingly, the viscosity behavior of the pigment preparations may also vary greatly depending on the particle shape. In order to obtain an ideal Newtonian viscosity behavior of the preparations, the particles should preferably have a spherical to cube-shaped (with flattened corners) shape.

As an exemplary selection of particularly preferred organic pigments, carbon black pigments, e.g. Gas or furnace carbon black; Monoazo and disazo pigments, in particular the Color Index Pigments Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow® 83, Pigment Yellow® 87, Pigment Yellow® 97, Pigment Yellow® 111, Pigment Yellow® 126, Pigment Yellow® 127, Pigment Yellow® 128, Pigment Yellow® 155, Pigment Yellow® 174, Pigment Yellow® 176, Pigment Yellow® 191, Pigment Yellow® 213, Pigment Yellow Pigment Red 219, Pigment Red 38, Red Pigment Red 144, Red Red Pigment 214, Pigment Red 242, Pigment Red 262, Pigment Red 266, Pigment Red 269, Pigment Red 274, Pigment Orange

13, Pigment Orange 34 or Pigment Brown 41; ß-naphthol and naphthol AS pigments, in particular the Color Index pigments Pigment Red 2, Pigment Red

3, Pigment Red 4, Pigment Red 5, Pigment Red 9, Pigment Red 12, Pigment Red

14, Pigment Red 53: 1, Pigment Red 112, Pigment Red 146, Pigment Red 147, Pigment Red 170, Pigment Red 184, Pigment Red 187, Pigment Red 188, Pigment Red 210, Pigment Red 247, Pigment Red 253, Pigment Red 256, Pigment Orange 5, Pigment Orange 38 or Pigment Brown 1; laked azo and metal complex pigments, in particular the Color Index pigments Pigment Red 48: 2, Pigment Red 48: 3, Pigment Red 48: 4, Pigment Red 57: 1, Pigment Red 257, Pigment Orange 68 or Pigment Orange 70; Benzimidazolinpigmente, in particular the Color Index Pigments Pigment Yellow 120, Pigment Yellow 151, Pigment Yellow 154, Pigment Yellow 175, Pigment Yellow 180, Pigment Yellow 181, Pigment Yellow 194, Pigment Red 175, Pigment Red 176, Pigment Red 185, Pigment Red 208, Pigment Violet 32, Pigment Orange 36, Pigment Orange 62, Pigment Orange 72 or Pigment Brown 25; Isoindolinone and

Isoindoline pigments, in particular the Color Index pigments Pigment Yellow 139 or Pigment Yellow 173; Phthalocyanine pigments, in particular the Color Index pigments Pigment Blue 15, Pigment Blue 15: 1, Pigment Blue 15: 2, Pigment Blue 15: 3, Pigment Blue 15: 4, Pigment Blue 15: 6, Pigment Blue 16, Pigment Green 7 or Pigment Green 36; Anthanthrone, anthraquinone, quinacridone, dioxazine, indanthrone, perylene, perinone and thioindigo pigments, in particular the Color Index Pigments Pigment Yellow 196, Pigment Red 122, Pigment Red 149, Pigment Red 168, Pigment Red 177, Pigment Red 179, Pigment Red 181, Pigment Red 207, Pigment Red 209, Pigment Red 263, Pigment Blue 60, Pigment Violet 19, Pigment Violet 23 or Pigment Orange 43; Triarylcarboniumpigmente, in particular the Color Index pigments Pigment Red 169, Pigment Blue 56 or Pigment Blue 61; Diketopyrrolopyrrolpigmente, in particular the Color Index pigments Pigment Red 254, Pigment Red 255, Pigment Red 264, Pigment Red 270, Pigment Red 272, Pigment Orange 71, Pigment Orange 73, Pigment Orange 81, call.

The organic pigment is preferably combined with carbon black and / or titanium dioxide.

Also suitable are laked dyes such as Ca, Mg, Al lacquers of dyes containing sulfonic acid and / or carboxylic acid groups.

Examples of suitable inorganic pigments are titanium dioxides, zinc sulfides, zinc oxides, iron oxides, magnetites, manganese iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, manganese titanium rutiles, cobalt oxides, mixed oxides of cobalt and aluminum, rutile mixed phase pigments, rare earth sulfides, spinels of cobalt with nickel and zinc , Spinels based on iron and chromium with copper zinc as well as manganese, bismuth vanadate and extender pigments. In particular, the Color Index pigments Pigment Yellow 184, pigment Yellow Yellow, Pigment Yellow Brown, Pigment Yellow Brown, Pigment Red Brown, Pigment Blue, Pigment Blue, Pigment Green, Pigment Green, Pigment Black, Pigment Black, and Pigment White. Preference is also often given to using mixtures of inorganic pigments. Mixtures of organic and inorganic pigments are also commonly used.

Instead of pigment dispersions can also be prepared dispersions containing as solids, for example, natural finely divided ores, minerals, difficult or insoluble salts, wax or plastic particles, dyes, crop protection and pest control, UV absorbers, optical brighteners and polymerization stabilizers.

Component (B) of the pigment preparations of the invention are customary dispersants suitable for the preparation of aqueous pigment dispersions and surfactants or mixtures of such substances. Usually, anionic, cationic, amphoteric or nonionic surfactant compounds are used therefor. Dispersing agents which have one or more medium- or long-chain hydrocarbon chains and, in some cases, those which have aromatic ring groups have proved particularly suitable. Of the large number of compounds, only a selection should be mentioned at this point, but without restricting the applicability of the compounds according to the invention to these examples. Examples are alkyl sulfates such as lauryl sulfate, stearyl sulfate or octadecyl sulfate, primary alkyl sulfonates such as dodecyl sulfonate, and secondary alkyl sulfonates, especially the C ₃ -C 17 alkanesulfonate sodium salt, alkyl phosphates, alkylbenzenesulfonates such as dodecylbenzenesulfonic acid, as well as all salts of these compounds. Furthermore, soya lecithin is suitable or condensation products of fatty acid and taurine or hydroxyethanesulfonic acid are used, as are alkoxylation products of alkylphenols,

Castor oil rosin esters, fatty alcohols, fatty amines, fatty acids and fatty acid amides, these alkoxylation products may likewise be endowed with ionic end groups, for example as sulfosuccinic acid half esters or as sulfonic acid, sulfuric and phosphoric acid esters, and their salts, the sulfonates, sulfates or phosphates. Also suitable are oxalkylated addition compounds which are obtained by reacting polyepoxides with amines or bisphenol A or bisphenol A derivatives with amines, likewise urea derivatives in a similar manner.

Also suitable are reaction products of substituted and unsubstituted relatively long- and shorter-chain alkylphenols and their polymeric derivatives, such as formaldehyde condensation products, the novolaks. Mention may also nonionic alkoxylated styrene-phenol condensates, which are obtained by addition of optionally substituted styrenes to optionally substituted phenols and reaction with ethylene oxide and / or propylene oxide, as well as their ionically modified derivatives, for example as sulfonic acid, sulfuric acid and phosphoric acid esters, and their salts, sulfonates, sulfates or phosphates. Also suitable as surface-active compounds of component (B) are lignosulfonates and polycondensates of naphthalenesulfonic acid and formaldehyde or of alkylarylsulfonic acids, haloarylsulfonic acid, sulfonated phenols or sulfonated naphthols with formaldehyde. Finally, polymeric dispersants, for example aqueous, preferably from 5 to 40 percent by weight, of acrylate resin solutions of dissolved polyacrylates which have been brought into solution by means of bases by neutralization of the vinylic acid components are also suitable. The polyacrylates used for this purpose are frequently copolymers which consist essentially of 30 to 80 mol% of monoalkylene aromatics and 20 to 70 mol% of acrylic and / or methacrylic acids and / or esters of acrylic and / or methacrylic acid. The polyacrylates used generally have number-average molar masses M _{n of} between 1000 and 100 000 g / mol, preferably 2000 to 50 000 g / mol.

Suitable components (C) are polyalkylene glycols of at least trivalent, for example tri-, tetra-, penta- or hexa-hydric, alcohols which are preferably branched and more preferably branched in a star shape. Star-branched compounds are understood to mean those having at least one quaternary aliphatic carbon atom. Examples of suitable alcohols are Glycerol, diglycerol, triglycerol, oligoglycerols, trimethylolethane, trimethylolpropane, 1, 2,3-hexanetriol, sorbitol, mannitol, pentaerythritol and dipentaerythritol. The alcohols mentioned are alkoxylated per mole with up to 1000 moles of alkylene oxide, preferably 4 to 200 moles, of alkylene oxide, such as ethylene oxide, propylene oxide, n-butylene oxide, isobutylene oxide, styrene oxide or a mixture thereof.

Particularly preferred as component (C) are compounds of the formula (1),

wherein

R ^1, R ^2, R ³ are independently hydrogen, a branched or unbranched C-ι-C2 ₀ alkyl or C3-C2o-cycloalkyl, branched or unbranched C2-C2o-alkenyl or C ₃ -C 2 ₀ -

Cycloalkenyl radical, a benzyl radical or a phenyl radical, preferably H,

CH ₃ or C ₂ H ₅ , and m is, on average, a number from 0 to 100, preferably from 1 to 60, particularly preferably 4 to 25, n averaging a number from 0 to 100, preferably from 0 to 60, particularly preferably 0 to 10, p is, on average, a number from 0 to 100, preferably from 0 to 60, particularly preferably 0 to 10, wherein the sum m + n + p is at least 1, preferably at least 4 and particularly preferably 15 to 30.

The compound of the formula (1) is prepared by alkoxylation of pentaerythritol with at least four times the molar amount of alkoxide. Thereby arise naturally mixtures with different long alkoxide chains, so that for the numbers m, n and p only average values can be given.

The polyglycol alkyl ether corresponding to the component (D) is preferably a compound of the formula (2)

R4-O- [cH _i -CH- θ] ^ R5

(2) wherein R ^{4 is} a substituted or unsubstituted, unbranched or preferably branched C 2 -C 20 -alkyl or C 3 -C 20 -cycloalkyl radical or a substituted or unsubstituted, branched or unbranched

C2-C ₂ o-alkenyl or C ₃ -C 2o-cycloalkenyl radical, where the substituents 1, 2, 3 or 4 radicals from the group halogen, aryl, aryl (Ci-C ₂ o) alkyl, C ₅ -C ₆ Cycloalkyl, hetaryl, hetaryl (C ₁ -C 20) alkyl or C ₁ -C 20 -alkoxy, q is a number from 1 to 200, preferably 50 to 120,

R ⁵ is H, XM or a substituted or unsubstituted, unbranched or, preferably, branched C ₂ -C ₂ o alkyl or C ₃ -C ₂ o-cycloalkyl radical or a substituted or unsubstituted, branched or unbranched C ₂ -C2o-alkenyl or C ₃ -C ₂ o-Cycloalkenylrest, wherein the substituents 1, 2, 3 or 4 radicals from the group

Halogen, aryl, aryl (C ₁ -C 20) alkyl, C ₅ -C ₆ -cycloalkyl, hetaryl, hetaryl (C ₁ -C 20) -alkyl or C ₁ -C 20 -alkoxy, where X is SO ₃ ^" , SO ₂ ^" , CH ₂ COO, PO ₃ ^{2 "} or PO ₃ M ^" , and

MH, a monovalent metal cation, a divalent metal cation, NH4 ⁺ , a secondary, tertiary or quaternary ammonium ion, or a

Combination of it, mean.

As component (E), hydrotropic retention agents are used. Suitable compounds are those which optionally also serve as solvents, or are of oligomeric or polymeric nature, for example formamide, urea, tetramethylurea, ε-caprolactam, ethylene glycol, propylene glycol, Diethylene glycol, triethylene glycol, polyethylene glycol, α-methyl-ω-hydroxy polyethylene glycol, dimethyl polyethylene glycol, dipropylene glycol, polypropylene glycol, Dimethylpolypropylenglykolether, copolymers of ethylene and propylene glycol, butyl glycol, methyl cellulose, glycerol, diglycerol, polyglycerol, N-methylpyrrolidone, 1, 3-diethyl -2-imidazolidinone, thiodiglycol, sodium benzenesulfonate, sodium xylenesulfonate, sodium toluenesulfonate, sodium cumene sulfonate, sodium dodecylsulfonate, sodium benzoate, sodium salicylate, sodium butylmonoglycol sulfate, cellulose derivatives, gelatin derivatives, polyvinylpyrrolidone, polyvinyl alcohol, polyvinylimidazole and Co and terpolymers of vinylpyrrolidone, vinyl acetate and vinylimidazole, in which case the

Polymers with vinyl acetate can be subjected to saponification to vinyl alcohol.

Component (F) corresponds to fats and oils of vegetable and animal origin, for example beef tallow, palm kernel fat, coconut oil, rapeseed oil, sunflower oil, linseed oil, palm oil, soybean oil, peanut oil and whale oil, cottonseed oil, corn oil, poppy oil, olive oil, castor oil, rapeseed oil, safflower oil, soybean oil , Thistle oil, sunflower oil, herring oil, sardine oil. Also, the saturated and unsaturated higher fatty acids are common additives, e.g. Palmitic, Cyprylic, capric, myristic, lauric, stearic, oleic, linoleic, linolenic, caproic, caprylic, arachidic, behenic, palmitoleic, gadoleic, erucic and ricinoleic acids and salts thereof.

As component (G), for example, cationic, anionic, amphoteric or nonionic compounds are used which promote pigment wetting (wetting agent). Thickeners, preservatives, viscosity stabilizers, grinding aids and fillers are also used. Further customary additives may be antisettling agents, light stabilizers, antioxidants, degasifiers / defoamers, foam-reducing agents, anti-caking agents and additives which favorably influence viscosity and rheology. As a viscosity modifier, for example, polyvinyl alcohol and cellulose derivatives are suitable. Water-soluble natural or synthetic resins and polymers as film formers or binders for increasing adhesion and abrasion resistance as well. As pH regulators, organic or inorganic bases and acids are used. Preferred organic bases are amines, such as ethanolamine, diethanolamine, triethanolamine, N, N-dimethylethanolamine, diisopropylamine, aminomethylpropanol or dimethylaminomethylpropanol. Preferred inorganic bases are sodium, potassium, lithium hydroxide or ammonia.

Water used to prepare the pigment preparations, component (H), is preferably used in the form of desalted or distilled water. Also drinking water (tap water) and / or water of natural origin can be used.

The present invention also provides a process for the preparation of the pigment preparations according to the invention, which comprises reacting component (A) in the form of powder, granules or aqueous presscake in the presence of water (H) and components (B), (C). and (D) dispersed, then optionally water (H), and optionally admixing one or more of components (E), (F) and (G) and optionally adjusting the resulting aqueous pigment dispersion with water (H) to the desired concentration. Preferably, the components (B), (C) and (D) and optionally one or more of the components (E), (F) and (G) are first mixed and homogenized, then the component (A) is stirred into the initially introduced mixture, wherein the pigment is pasted and predispersed. Depending on the grain hardness of the pigments used, it is then optionally finely dispersed or finely divided with cooling with the aid of a grinding or dispersing unit. For this purpose, agitators, dissolvers (sawtooth), rotor-stator mills, ball mills, stirred ball mills such as sand and bead mills, high-speed mixers, kneaders, roller mills or high performance bead mills can be used. The fine dispersion or grinding of the pigments is carried out to the desired particle size distribution and can be carried out at temperatures ranging from 0 to 100 ⁰ C, preferably at a temperature between 10 and 7O ⁰ C, preferably at 20 to 60 ⁰ C. Following to fine dispersion, the pigment preparation can be further diluted with water (H), preferably deionized or distilled water.

The pigment preparations according to the invention are suitable for pigmenting and dyeing natural and synthetic materials of all kinds, in particular aqueous paints, dispersion and enamel paints (dispersion paints). Furthermore, the pigment preparations according to the invention are suitable for coloring macromolecular materials of all kinds, e.g. of natural and synthetic fiber materials, preferably cellulose fibers, also for paper pulp dyeing as well as for laminate dyeing. Other applications include the production of

Printing inks, in this case for example textile printing, flexoprinting, decorative printing or gravure printing inks, wallpaper paints, water-dilutable paints, wood protection systems, viscose spin dyes, paints, sausage casings, seeds, fertilizers, glass, in particular glass bottles, and for mass coloration of roof tiles, for coloring for plasters, Concrete, wood stains, crayon mines,

Fibers, waxes, paraffins, brushes, pastes for pens, chalks, detergents and cleaners, shoe care products, latex products, abrasives and for coloring plastics or high molecular weight materials of all kinds. High molecular weight organic materials are, for example, cellulose ethers and esters, such as ethylcellulose , Nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins, such as polymerization or condensation resins, eg Aminoplasts, in particular urea- and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenoplasts, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic acid esters, polyamides, polyurethanes or polyesters, rubber, casein, latices, silicone, silicone resins, individually or in Mixture.

Furthermore, the pigment preparations according to the invention are suitable for the production of printing inks for use in all conventional ink-jet printers, in particular for those based on the bubble jet or piezo process. These printing inks can be used to print on paper, as well as natural or synthetic fiber materials, films and plastics. In addition, the pigment preparations according to the invention can be used for printing various types of coated or uncoated substrate materials, for example for printing on board, cardboard, wood and wood-based materials, metallic materials, semiconductor materials, ceramic materials, glasses, glass and ceramic fibers, inorganic materials, concrete, leather, foods, cosmetics, skin and hair , The substrate material may be two-dimensional flat or spatially extended, ie be designed in three dimensions and both completely or only partially printed or coated.

The pigment preparations of the present invention are also useful as colorants in electrophotographic toners and developers, e.g. One- or two-component powder toners (also called one- or two-component developer), magnetic toner, liquid toner, latextoner, polymerization toner and special toner. Typical toner binders here are polymerization, polyaddition and polycondensation resins, such as styrene, styrene acrylate, styrene butadiene, acrylate, polyester, phenolic epoxy resins, polysulfones,

Polyurethanes, individually or in combination, as well as polyethylene and polypropylene, which may contain other ingredients such as charge control agents, waxes or flow aids, or be modified afterwards with these additives.

Furthermore, the pigment preparations according to the invention are suitable as colorants for powders and powder coatings, in particular for triboelectrically or electrokinetically sprayable powder coatings, which are used for surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.

In addition, the pigment preparations of the present invention are colorants in inks, preferably ink-jet inks, such as aqueous or non-aqueous (solvent based), microemulsion inks, UV curable inks, and inks that function by the hot-melt process , suitable. Ink-jet inks generally contain a total of 0.5 to 15 wt .-%, preferably 1, 5 to 8 wt .-%, (calculated dry) of the pigment preparation according to the invention. Microemulsion inks are based on organic solvents, water and possibly an additional hydrotropic substance (interface mediator). Microemulsion inks contain 0.5 to 15 wt .-%, preferably 1, 5 to 8 wt .-%, of the pigment preparation according to the invention, 5 to 99 wt .-% water and 0.5 to 94.5 wt .-% organic solvent and / or hydrotrope compound. "Solvent-based" ink-jet inks preferably contain 0.5 to 15% by weight of the pigment preparation according to the invention, 85 to 99.5% by weight of organic solvent and / or hydrotropic compounds. UV-curable inks contain substantially 0.5 to 30 wt .-% of the pigment preparation according to the invention, 0.5 to 95 wt .-% water, 0.5 to 95 wt .-% of an organic solvent or solvent mixture, 0.5 to 50 wt .-% of a radiation-curable binder and optionally 0 to 10 wt .-% of a photoinitiator. Hot-melt inks are usually based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and liquid when heated, the preferred melting range between about 6O ⁰ C and 140 ⁰ C is about. For example, hot-melt ink-jet inks consist essentially of 20 to 90% by weight of wax and 1 to 10% by weight of the pigment preparation of the invention. Furthermore, 0 to 20 wt .-% of an additional polymer (as a "dye remover"), 0 to 5 wt .-% dispersing aid, 0 to 20 wt .-% viscosity modifier, 0 to 20 wt .-% plasticizer, 0 to 10 wt % Of tackiness additive, 0 to 10% by weight of transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight of antioxidant.

In addition, the pigment preparations according to the invention are also suitable as colorants for "color filter" for "Fiat panel displays", both for additive and for the subtractive color generation, also for "photo-resists", as well as colorants for electronic inks (" Electronic Inks "or" e-inks ") or electronic paper (" Electronic Paper "or" e-paper ").

Examples

Evaluation of a pigment preparation:

The color strength and hue were determined according to DIN 55986. For the "rub-out test", the emulsion paint or the paint was mixed with the pigment dispersion applied to a paint card. Subsequently, rubbed with the finger on the lower part of the paint card. Incompatibility was when the rubbed area was then stained more vividly or lighter than the adjacent untreated area (the rub-out test is described in DE-A-2 638 946.) The coloristic data and compatibilities with the The media to be dyed were determined on the basis of up to eight different commercial white dispersions and up to two different commercially available paints The evaluation of the resistance to drying was carried out by filling the pigment preparation in a well of a spot plate

Evaluation of the dispersion was carried out after 1, 4, 8, 24 and 48 hours. Skin formation and general drying were assessed. The viscosity was measured using a cone-plate viscometer (Roto Visco 1) Haake at 2O ⁰ C (titanium cone: 0 60 mm, 1 °), the dependence of viscosity on the shear rate in a range between 0 and 200 s ^{'1 was} examined. The viscosities were measured at a shear rate of 60 s ^-1 .

To evaluate the storage stability of the dispersions, the viscosity was measured directly after production of the preparation and also after four weeks of storage at 5O ⁰ C and after storage in a climate chamber with <O ⁰ C.

Preparation of a pigment preparation:

The pigment, either as a powder, granules or as a press cake, was made into a paste together with the dispersants and the other additives in deionized water and then with a dissolver (eg from VMA Getzmann GmbH, type AE3-M1) or another suitable apparatus homogenized and predispersed. Subsequent fine dispersion was carried out with the aid of a bead mill (for example with AE3-M1 from VMA-Getzmann) or another suitable dispersing unit, grinding with silver quartzite beads or zirconium mixed oxide beads of size d = 1 mm with cooling to the desired color intensity and colorimetry. The dispersion was then deionized with water to the desired Adjusted final pigment concentration, the grinding media separated and the pigment preparation isolated.

The pigment preparations described in the following examples were prepared by the method described above, wherein the constituents in the stated amounts were used so that 100 parts of the respective pigment preparation are formed. In the following examples, parts are parts by weight.

Example 1 48 parts Component (A), Cl. Pigment Yellow 74

4 parts of component (B), ionically modified tristyrylphenyloxyethylate

5 parts of component (C), compound of formula (1) where n = 0, m = 16, p = 4,

R ³ = CH ₃ ,

5 parts of component (D), R ⁴ = isotridecyl, q = 100, R ⁵ = H 1 part of component (F), vegetable oil

4 parts component (G), rheology additives

0.9 parts component (G), preservative residue component (H), water

The pigment preparation has a high color strength and is particularly flocculation-stable. In six different commercially available white dispersions it can be incorporated very easily with easy dispersibility. In all cases, the rub-out test shows no color intensity differences in comparison between the rubbed area and the untreated area. Thus, the preparation is very well tolerated to the tested dispersions. The

Pigment preparation has excellent rheological properties, proves to be well flowable and storage stable. The viscosity after preparation is 0.58 Pa s. Furthermore, the preparation has a good resistance to drying, since it begins to dry only after 24 hours.

Example 2

70 parts component (A), Cl. Pigment Red 101

3 parts of component (B), ionically modified tristyrylphenyloxyethylate 5 parts of component (C), compound of formula (1) with R ³ = CH ₃ , n = 0, m = 16, p = 4 5 parts of component (D), R ⁴ = isotridecyl, q = 100, R ⁵ = H

2 parts component (G), rheology additives 0.9 parts component (G), preservative residue Component (H), water

The pigment preparation has a coloration corresponding to the standard dispersion and is particularly flocculation-stable. In six different white dispersions it can be incorporated very easily with easy dispersibility. In all cases, the rub-out test shows no color intensity differences in comparison between the rubbed area and the untreated area. Thus, the preparation is very well tolerated to the tested dispersions. The pigment preparation has excellent theological properties for inorganic pigment pastes and has good flowability and storage stability. The viscosity after preparation is 2.3 Pa s. Furthermore, the preparation has a good resistance to drying, since it begins to dry only after 24 hours.

Comparative Example 2a

70 parts component (A), Cl. Pigment Red 101

3 parts of component (B), ionically modified tristyrylphenyloxyethylate 10 parts of component (E), triethylene glycol

2 parts component (G), rheology additives 0.9 parts component (G), preservative

Residual component (H), water.

Example 3

70 parts component (A), Cl. Pigment Brown 24 3 parts Component (B), ionically modified tristyrylphenyloxyethylate

3 parts Component (B), fatty acid oxyethylate, ionically modified

5 parts of component (C), compound of formula (1) where R ¹ = H, R ² = CH ₃ , n = 20, m = 5, p = 0 10 parts of component (D), R ⁴ = isotridecyl, q = 100, R ⁵ = H 1 part of component (G), rheology additive

0.9 parts component (G), preservative residue component (H), water

The pigment preparation has a coloration corresponding to the standard dispersion and is particularly flocculation-stable. In six different white dispersions it can be incorporated very easily with easy dispersibility. In all cases, the rub-out test shows no color intensity differences in comparison between the rubbed area and the untreated area. Thus, the preparation is very well tolerated to the tested dispersions. The pigment preparation has excellent theological properties for inorganic pigment pastes and proves to be readily flowable and storage-stable. The viscosity after preparation is 1.9 Pa s. Furthermore, the preparation has a good resistance to drying, since it begins to dry only after 24 hours.

Example 4

62 parts component (A), Cl. Pigment Blue 28 4 parts component (B), tristyrylphenyloxyethylate

5 parts of component (C), compound of formula (1) where R ³ = CH ₃ , n = 0, m = 16, p = 4

5 parts component (D), R ⁴ = isotridecyl, q = 100, R ⁵ = H

2.5 parts of component (E), polyvinylpyrrolidone 1 part of component (G) Rheology additive

0.9 parts component (G), preservative

Residual component (H), water

The pigment preparation has a color matching the standard. In six different white dispersions it can be incorporated very easily with easy dispersibility. In all cases, the rub-out test shows no color intensity differences in comparison between the rubbed area and the untreated area, so that no flocculation phenomena occur can be detected. Thus, the preparation is universally compatible with the tested dispersions. The pigment preparation has excellent rheological properties, proves to be readily flowable and is storage-stable. The viscosity after preparation is 2.0 Pa s. Furthermore, the preparation has a good resistance to drying since it begins to dry after 24 hours.

Example 5

3 parts Component (B), fatty acid oxyethylate, ionically modified

5 parts of component (C), compound of formula (1) where R ¹ = H, R ² = CH ₃ , n = 20, m = 5, p = 0

5 parts component (D), R ⁴ = isotridecyl, q = 100, R ⁵ = H 2.5 parts component (E), polyvinylpyrrolidone

1 part of component (G) Rheology additive

0.9 parts component (G), preservative

Residual component (H), water

The pigment preparation has a coloration corresponding to the standard dispersion and is particularly flocculation-stable. In six different white dispersions it can be incorporated very easily with easy dispersibility. In all cases, the rub-out test shows no color intensity differences in comparison between the rubbed area and the untreated area. Thus, the preparation is very well tolerated to the tested dispersions. The

Pigment preparation has excellent theological properties for inorganic pigment pastes and proves to be readily flowable and storage-stable. The viscosity after preparation is 1.9 Pa s. Furthermore, the preparation has a good resistance to drying, since it begins to dry only after 24 hours.

Claims

claims:

1. Aqueous pigment preparation containing

(C) a trihydric or higher alkoxylated alcohol,

(D) a polyglycol alkyl ether,

(E) optionally hydrotrope oligomers and / or polymers,

(F) optionally fats, oils or fatty acids, (G) optionally further customary for the preparation of aqueous pigment dispersions additives, and (H) water.

2. Pigment preparation according to claim 1, characterized in that the organic pigment of component (A) is a monoazo, disazo, laked azo, ß-naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigment or a polycyclic pigment from the group of phthalocyanine, quinacridone, perylene, perinone, thioindigo, anthanthrone, anthraquinone, flavanthrone, indanthrone, isoviolanthrone, pyranthrone, dioxazine, quinophthalone, isoindolinone, Isoindoline and Dtketopyrrolopyrrol pigments or carbon blacks.

3. Pigment preparation according to claim 1 or 2, characterized in that the alcohol of component (C) branched, in particular star-branched, is.

4. Pigment preparation according to one or more of claims 1 to 3, characterized in that the alcohol of component (C) from the group glycerol, diglycerol, triglycerol, oligoglycerol, trimethylolethane, trimethylolpropane, 1, 2,3-hexanetriol, sorbitol, mannitol , Pentaerythritol and

Dipentaerythritol is selected and alkoxylated per mole with up to 1000 moles of alkylene oxide.

5. Pigment preparation according to one or more of claims 1 to 4, characterized in that component (C) is a compound of formula (1),

(1)

wherein

R ¹ , R ² , R ^{3 are} independently hydrogen, C ₁ -C ₂ O-AlkYl, C ₃ -C ₂ O-

Cycloalkyl, C ₂ -C ₂₀ alkenyl, C ₃ -C ₂ o-cycloalkenyl, phenyl or benzyl, m is a number from 0 to 100 n on average a number from 0 to 100 p is on average a number from 0 to 100, where the sum m + n + p is at least 1.

6. Pigment preparation according to one or more of claims 1 to 5, characterized in that component (D) is a compound of formula (2),

R4-θ {cH ^ -CH _i -θ] ^ R5

(2) wherein

R ⁴ is a substituted or unsubstituted, unbranched or, preferably, branched C2-C ₂ o alkyl or C ₃ -C ₂ o-cycloalkyl radical or a substituted or unsubstituted, branched or unbranched C ₂ -C ₂ o-alkenyl or C ₃ - C ₂₀ -cycloalkenyl radical, where the substituents 1, 2, 3 or 4 radicals from the group halogen, aryl, Aryl _(Ci-C2o) alkyl, C ₅ -C ₆ -cycloalkyl, hetaryl, hetaryl (C ₂₀₎ alkyl or Ci-C _2O -alkoxy, q is a number from 1 to 200, preferably 50 to 120, is

R ⁵ is H, XM or a substituted or unsubstituted, unbranched or, preferably, branched _C2-C2o-alkyl or _{C3-C2o-cycloalkyl} radical or a substituted or unsubstituted, branched or unbranched C ₂ -C ₂ o-alkenyl, or C3-C-2o-Cycloalkenylrest, wherein the substituents 1, 2, 3 or 4 radicals from the group halogen, aryl, aryl (Ci-C ₂ o) alkyl, Cs-Ce-cycloalkyl, hetaryl, hetaryl (Ci-C ₂ o) alkyl or Ci -C _2O -alkoxy, said

X SO ₃ ^" , SO ₂ ^' , CH ₂ COO, PO ₃ ^2' or PO ₃ M ^" , and

M is H, a monovalent metal cation, a divalent metal cation, NH /, a secondary, tertiary or quaternary ammonium ion, or a combination thereof.

7. Pigment preparation according to one or more of claims 1 to 6, containing 5 to 80 wt .-% of component (A).

8. Pigment preparation according to one or more of claims 1 to 7, containing 0.1 to 30 wt .-% of component (C).

9. Pigment preparation according to one or more of claims 1 to 8, comprising component

(A) 5 to 80% by weight,

(B) 0.1 to 30% by weight,

(C) 0.1 to 30% by weight,

(D) 0.1 to 20% by weight,

(E) 0 to 20% by weight,

(F) O to 10% by weight,

(G) 0 to 30% by weight,

(H) balance water, in each case based on the total weight of the pigment preparation.

10. A process for preparing a pigment preparation according to at least one of claims 1 to 9, characterized in that the component (A) in the form of powder, granules or aqueous presscake in the presence of water (H) and the components (B), ( C) and (D) dispersed, then optionally water (H), and optionally one or more of the components (E) ₁ (F) and (G) admixed and optionally the resulting aqueous pigment dispersion with water (H).

11. Use of a pigment preparation according to one or more of claims 1 to 9 for pigmenting natural or synthetic materials.

12. Use according to claim 11 for pigmenting aqueous paints, dispersion and enamel paints, water-based paints, wallpaper colors and printing inks.

13. Use according to claim 11 for pigmenting natural and synthetic fiber materials, cellulose fibers, pulp dyeing and laminate dyeing and for the production of printing inks, ink-jet inks, electrophotographic toners, powder coatings, color filters, electronic inks and "electronic paper", color filters, Wood preservation systems, viscose spin dyeing, sausage intestines, seeds, fertilizers, glass bottles, and for mass coloration of roof tiles, for coloring for plasters, concrete, wood stains, colored pencil lead, felt pens, waxes, paraffins, tusche, pastes for pens, chalks, detergents and cleaners, Shoe polishes, latex products, abrasives and for coloring plastics.